Oxidative Amidation of Nitroalkanes with Amine Nucleophiles using Molecular Oxygen and Iodine.
Angew Chem Int Ed Engl
; 54(44): 12986-90, 2015 Oct 26.
Article
em En
| MEDLINE
| ID: mdl-26349836
The formation of amides and peptides often necessitates powerful yet mild reagent systems. The reagents used, however, are often expensive and highly elaborate. New atom-economical and practical methods that achieve such goals are highly desirable. Ideally, the methods should start with substrates that are readily available in both chiral and non-chiral forms and utilize cheap reagents that are compatible with a wide variety of functional groups, steric encumberance, and epimerizable stereocenters. A direct oxidative method was developed to form amide and peptide bonds between amines and primary nitroalkanes simply by using I2 and K2 CO3 under O2 . Contrary to expectations, a 1:1 halogen-bonded complex forms between the iodonium source and the amine, which reacts with nitronates to form α-iodo nitroalkanes as precursors to the amides.
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Base de dados:
MEDLINE
Assunto principal:
Oxigênio
/
Alcanos
/
Amidas
/
Aminas
/
Iodo
/
Nitrocompostos
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article